[144] Upwork Inc. SEC Filing

Rhea-AI Filing Summary

Form 144 notice from an insider at Upwork Inc. (UPWK) discloses a proposed sale of 1,690 common shares through Morgan Stanley Smith Barney on 08/29/2025 with an aggregate market value of $25,197.90. The securities were acquired as Restricted Stock Units on 08/18/2025 and payment was marked N/A. The filing also lists three recent sales by the same person, David Bottoms: 2,060 shares on 08/18/2025 (gross $28,504.22), 9,000 shares on 08/08/2025 (gross $115,937.10), and 11,562 shares on 06/18/2025 (gross $156,149.43). The notice includes the required attestation that the seller lacks undisclosed material adverse information.

Positive

• Regulatory compliance: The filing includes broker details and required attestation under Rule 144
• Transparent disclosure: Acquisition type (RSUs), acquisition dates, and gross proceeds for recent sales are itemized

Negative

• Insider selling activity: Multiple sales totaling 22,622 shares in recent months could raise investor questions about insider liquidity
• Relative concentration of recent sales: The three prior sales include larger blocks (9,000 and 11,562 shares), which may be viewed negatively absent contextual company information

Insights

Securities Analyst

TL;DR: Insider sales disclosed; sizes suggest routine liquidity rather than a single large, unexplained disposition.

The filing documents a planned, small block sale of 1,690 shares acquired as RSUs and executed through Morgan Stanley Smith Barney, accompanied by multiple recent sales by the same insider totaling 22,622 shares over the past months. From a securities-transaction perspective, the filing meets Rule 144 notice requirements and provides clear acquisition and sale dates and gross proceeds for recent trades. Without company-level context or material nonpublic disclosures, these transactions read as scheduled or opportunistic sales rather than signs of an event-driven transfer.

Corporate Governance Expert

TL;DR: Compliance appears intact; disclosure includes attestation required under Rule 144.

The Form 144 includes the representation that the seller is unaware of undisclosed material adverse information and shows the relationship to the broker and mechanics of acquisition (RSUs). The presence of multiple sales in a short timeframe merits governance attention for patterns but the document itself provides the standard confirmations and broker details necessary for regulatory transparency.

Form 144 Filer Information	UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 144 NOTICE OF PROPOSED SALE OF SECURITIES PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OF 1933
FORM 144

144: Filer Information

Filer CIK
Filer CCC
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer

SEC File Number

Address of Issuer

Phone

Name of Person for Whose Account the Securities are To Be Sold

See the definition of "person" in paragraph (a) of Rule 144. Information is to be given not only as to the person for whose account the securities are to be sold but also as to all other persons included in that definition. In addition, information shall be given as to sales by all persons whose sales are required by paragraph (e) of Rule 144 to be aggregated with sales for the account of the person filing this notice.

Relationship to Issuer

144: Securities Information

Title of the Class of Securities To Be Sold	Name and Address of the Broker	Number of Shares or Other Units To Be Sold	Aggregate Market Value	Number of Shares or Other Units Outstanding	Approximate Date of Sale	Name the Securities Exchange
Common	Morgan Stanley Smith Barney LLC Executive Financial Services 1 New York Plaza 8th Floor New York NY 10004	1690	25197.90	132606579	08/29/2025	NASDAQ

Furnish the following information with respect to the acquisition of the securities to be sold and with respect to the payment of all or any part of the purchase price or other consideration therefor:

144: Securities To Be Sold

Title of the Class	Date you Acquired	Nature of Acquisition Transaction	Name of Person from Whom Acquired	Is this a Gift?	Date Donor Acquired	Amount of Securities Acquired	Date of Payment	Nature of Payment *
Common	08/18/2025	Restricted Stock Units	Issuer			1690	08/18/2025	N/A

* If the securities were purchased and full payment therefor was not made in cash at the time of purchase, explain in the table or in a note thereto the nature of the consideration given. If the consideration consisted of any note or other obligation, or if payment was made in installments describe the arrangement and state when the note or other obligation was discharged in full or the last installment paid.

Furnish the following information as to all securities of the issuer sold during the past 3 months by the person for whose account the securities are to be sold.

144: Securities Sold During The Past 3 Months

Name and Address of Seller	Title of Securities Sold	Date of Sale	Amount of Securities Sold	Gross Proceeds
DAVID BOTTOMS 530 Lytton Ave, Suite 301 Palo Alto CA 94301	Common	08/18/2025	2060	28504.22
DAVID BOTTOMS 530 Lytton Ave, Suite 301 Palo Alto CA 94301	Common	08/08/2025	9000	115937.10
DAVID BOTTOMS 530 Lytton Ave, Suite 301 Palo Alto CA 94301	Common	06/18/2025	11562	156149.43

144: Remarks and Signature

Remarks

Date of Notice

Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1

ATTENTION:

The person for whose account the securities to which this notice relates are to be sold hereby represents by signing this notice that he does not know any material adverse information in regard to the current and prospective operations of the Issuer of the securities to be sold which has not been publicly disclosed. If such person has adopted a written trading plan or given trading instructions to satisfy Rule 10b5-1 under the Exchange Act, by signing the form and indicating the date that the plan was adopted or the instruction given, that person makes such representation as of the plan adoption or instruction date.

Signature

ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)

FAQ

What does this UPWK Form 144 disclose about the planned sale?

It discloses a proposed sale of 1,690 common shares via Morgan Stanley Smith Barney on 08/29/2025 with an aggregate market value of $25,197.90.

Who is the person selling the shares in the UPWK filing?

The filing identifies prior sales by David Bottoms and the proposed sale appears associated with that account; broker information is provided.

How were the securities being sold acquired according to the filing?

The securities were acquired as Restricted Stock Units (RSUs) on 08/18/2025 and the amount listed is 1,690 shares.

What recent sales by the insider are included in the filing?

The filing lists sales of 2,060 shares (gross $28,504.22) on 08/18/2025, 9,000 shares (gross $115,937.10) on 08/08/2025, and 11,562 shares (gross $156,149.43) on 06/18/2025.

Does the filing state the seller has undisclosed material information?

By signing the notice the seller represents they do not know any material adverse information about the issuer that has not been publicly disclosed.